JP2004508309A5 - - Google Patents
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- Publication number
- JP2004508309A5 JP2004508309A5 JP2002524317A JP2002524317A JP2004508309A5 JP 2004508309 A5 JP2004508309 A5 JP 2004508309A5 JP 2002524317 A JP2002524317 A JP 2002524317A JP 2002524317 A JP2002524317 A JP 2002524317A JP 2004508309 A5 JP2004508309 A5 JP 2004508309A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- producing
- base
- toluenesulfonyloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 2
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 claims 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
Claims (1)
に従って、a) 化学式IIIの化合物と化学式IVの2-メチル-2-プロペン-1-オールを塩基存在下で、1,3-双極子環化付加反応させ、化学式Vの中間体を製造する段階、及び
b) 化学式Vの中間体及び化学式VIの化合物を、塩基存在下で触媒が存在または存在しない状態で反応させる段階を含む、請求項1に記載の5-ベンジルオキシメチル-1,2-イソオキサゾリン誘導体の製造方法。Scheme 1
A) a step of producing an intermediate of formula V by subjecting a compound of formula III and 2-methyl-2-propen-1-ol of formula IV to 1,3-dipolar cycloaddition reaction in the presence of a base ,as well as
2. The 5-benzyloxymethyl-1,2-isoxazoline according to claim 1, comprising the step of reacting the intermediate of formula V and the compound of formula VI in the presence of a base with or without a catalyst. A method for producing a derivative.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2000-0052917A KR100392072B1 (en) | 2000-09-07 | 2000-09-07 | 5-Benzyloxymethyl-1,2-isoxazoline Derivatives Which Possess Weeding Activity |
| PCT/KR2001/001500 WO2002019825A1 (en) | 2000-09-07 | 2001-09-05 | Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004508309A JP2004508309A (en) | 2004-03-18 |
| JP2004508309A5 true JP2004508309A5 (en) | 2005-04-07 |
| JP3968012B2 JP3968012B2 (en) | 2007-08-29 |
Family
ID=19687824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002524317A Expired - Lifetime JP3968012B2 (en) | 2000-09-07 | 2001-09-05 | 5-Benzyloxymethyl-1,2-isoxazoline derivatives having herbicidal activity |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6838416B2 (en) |
| JP (1) | JP3968012B2 (en) |
| KR (1) | KR100392072B1 (en) |
| CN (1) | CN1303081C (en) |
| AU (2) | AU8629401A (en) |
| WO (1) | WO2002019825A1 (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100392072B1 (en) * | 2000-09-07 | 2003-07-22 | 한국화학연구원 | 5-Benzyloxymethyl-1,2-isoxazoline Derivatives Which Possess Weeding Activity |
| IL164487A0 (en) * | 2002-04-25 | 2005-12-18 | Basf Ag | 3-Heteroaryl substituted 5-methyloxymethyl isoxazolines used as herbicides |
| KR100814420B1 (en) | 2007-06-22 | 2008-03-18 | (주)목우연구소 | Uses of herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives |
| US8445409B2 (en) * | 2007-06-22 | 2013-05-21 | Moghu Research Center Ltd. | Use of 5-benzyloxymethyl-1,2-isoxazoline derivatives as a herbicide |
| AU2012308659B2 (en) | 2011-09-13 | 2017-05-04 | Monsanto Technology Llc | Methods and compositions for weed control |
| AU2012308686B2 (en) | 2011-09-13 | 2018-05-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| MX348495B (en) | 2011-09-13 | 2017-06-14 | Monsanto Technology Llc | Methods and compositions for weed control. |
| KR101093102B1 (en) | 2011-10-04 | 2011-12-13 | (주)목우연구소 | Phenylisoxazoline compound having herbicidal activity and uses thereof |
| KR101201203B1 (en) | 2012-04-02 | 2012-11-15 | (주)목우연구소 | Method for Manufacturing High Purity Methiozolin |
| EP2900660B1 (en) * | 2012-09-25 | 2018-01-17 | Bayer CropScience AG | Herbicidal and fungicidal 3-heteroarylisoxazolin-5-carboxamides and 3-heteroarylisoxazolin-5-thioamides |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| KR101708208B1 (en) | 2015-05-29 | 2017-02-21 | 한국화학연구원 | Chiral (S)-(4,5-dihydroisoxazole-5-yl)carboxylate derivatives and asymmetric synthesis thereof |
| JP2021073168A (en) * | 2018-03-08 | 2021-05-13 | 石原産業株式会社 | Herbicidal composition |
| WO2019243101A1 (en) | 2018-06-20 | 2019-12-26 | Basf Se | Method for controlling herbicide resistant or tolerant weeds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3809765A1 (en) * | 1988-03-23 | 1989-10-05 | Basf Ag | ISOXAZOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| GB9110858D0 (en) * | 1991-05-20 | 1991-07-10 | Shell Int Research | Herbicidal compounds |
| JPH09328477A (en) * | 1996-06-10 | 1997-12-22 | Sankyo Co Ltd | Herbicidal isoxazoline derivative |
| KR100392072B1 (en) * | 2000-09-07 | 2003-07-22 | 한국화학연구원 | 5-Benzyloxymethyl-1,2-isoxazoline Derivatives Which Possess Weeding Activity |
-
2000
- 2000-09-07 KR KR10-2000-0052917A patent/KR100392072B1/en active IP Right Grant
-
2001
- 2001-09-05 AU AU8629401A patent/AU8629401A/en active Pending
- 2001-09-05 JP JP2002524317A patent/JP3968012B2/en not_active Expired - Lifetime
- 2001-09-05 WO PCT/KR2001/001500 patent/WO2002019825A1/en active IP Right Grant
- 2001-09-05 CN CNB01815140XA patent/CN1303081C/en not_active Expired - Fee Related
- 2001-09-05 AU AU2001286294A patent/AU2001286294B2/en not_active Ceased
- 2001-09-05 US US10/363,808 patent/US6838416B2/en not_active Expired - Lifetime
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